Protonated Chiral 1,2-Diamine Organocatalysts for N-Selective Nitroso Aldol Reaction

The introduction of nitrogen to carbonyl groups is considered both challenging and highly desirable by those who work in the field organic synthesis. In this study, a diphenylethylenediamine-derived catalyst demonstrating N-selectivity was designed using quantum calculation for nitroso aldol reaction. reductive monoalkylation (R,R)-(+)-1,2-diphenylethylenediamine afforded an chiral diamine high yield. expected reaction mechanism determined, product solvent conditions were optimized through calculations. results revealed that enantioselectivity determined hydrogen bond between alkyl substituent oxygen aromatic aldehyde on ammonium moiety. found proceed optimally presence 5 mol % at −10 °C brine. Using these conditions, eco-friendly performed which cyclohexanone formed enamine. Nitrosobenzene, activated bonding with catalyst, used minimize steric hindrance reactant, resulting enantioselectivity. A (98% ee) obtained 95% developed study provides less expensive more environmentally friendly alternative